Welcome to Season 14, Episode 9 of Notes to My Legal Self, the in-house counsel podcast on AI, contracting, and the future of legal work.
Host Olga V. Mack talks with Cherryn-Paige Bissett, Internal Commercial Counsel at LegalSifter, about what to automate in contracting and what still needs a lawyer's judgment. With over 20 years as a commercial attorney, Cherryn shares her ""automate 80%, own 20%"" approach: use AI and playbooks to cut through contract noise, then focus your time on the risks that matter.
This legal tech and legal operations conversation is for in-house lawyers, corporate counsel, and anyone who wants to close deals faster without taking on unnecessary risk.
In this episode, you'll learn:
- How AI contract playbooks build consistency and reduce contract noise
- What separates a useful playbook from one that becomes rigid or ignored
- When to step outside the playbook, including new AI provisions in NDAs
- Which contracting decisions still require human judgment
- How to weigh possibility vs. probability when deciding which risks to push back on
- How a one-page contract primer can speed up negotiations
Timestamps:
00:00 Introduction
00:44 Meet Cherryn Bissett
01:33 From LegalSifter customer to in-house counsel
02:29 Automate 80%, own 20%
03:50 Cutting through contract noise
05:28 Building playbooks that scale across teams
07:35 When to step outside the playbook
09:46 AI provisions showing up in NDAs
10:31 When playbooks slow the business down
12:07 Where AI creates real value in contracting
14:51 Decisions that still need human judgment
18:02 How to be fast and accurate under pressure
20:12 Safest legal answer vs. best business decision
22:32 Skills that will set in-house lawyers apart
24:17 Final takeaway
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